Ammonia → HCID 86609421, compound

HRID 1171656Notes

Reaction equation

HRID 1171656 reaction equation
Cl.[C:2]([S:5][CH:6]1[CH2:11][CH2:10][N:9]([CH:12]([C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][C:19]=2[F:24])[C:13]([CH:15]2[CH2:17][CH2:16]2)=[O:14])[CH2:8]/[C:7]/1=[CH:25]\[C:26]1[CH:30]=[CH:29][N:28]([CH2:31][C:32]([OH:34])=O)[N:27]=1)(=[O:4])[CH3:3].ClC(OCC(C)C)=O.[NH3:43].C(=O)([O-])O.[Na+]>ClCCl.C(N(CC)CC)C>[C:2]([S:5][CH:6]1[CH2:11][CH2:10][N:9]([CH:12]([C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][C:19]=2[F:24])[C:13]([CH:15]2[CH2:16][CH2:17]2)=[O:14])[CH2:8]/[C:7]/1=[CH:25]\[C:26]1[CH:30]=[CH:29][N:28]([CH2:31][C:32](=[O:34])[NH2:43])[N:27]=1)(=[O:4])[CH3:3]

Participants

7

Reactant 4

HCID 222AmmoniaHCID 62365Isobutyl chloroformateHCID 516892Sodium BicarbonateHCID 86609418HCID 86609418, compound

Product 1

HCID 86609421HCID 86609421, compoundYield 42%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8471TriethylamineSolvent

Procedure

To a solution of (E)-4-(acetylsulfanyl)-3-{[1-(carboxymethyl)-1H-pyrazol-3-yl]methylidene}-1-[2-cyclopropyl-1-(2-fluorophenyl)-2-oxoethyl]piperidine hydrochloride (190 mg) in dichloromethane (15 ml) were added isobutyl chloroformate (0.06 ml) and triethylamine (0.18 ml) under ice-cooling, and the resulting mixture was stirred at the same temperature for 30 minutes. To this reaction mixture was added 28% aqueous ammonia solution (0.03 ml), and the resulting mixture was stirred at room temperature for 45 minutes. After stirring, saturated aqueous sodium hydrogencarbonate solution was added to the reaction mixture and extracted with dichloromethane. The extract was dried over anhydrous magnesium sulfate. The solvent was removed in vacuo, and the residue was purified by chromatography on a silica gel column using a mixed solvent of methanol and dichloromethane (1:19) as the eluent to afford the title compound (80 mg, yield: 42%) as a yellow oil.

Workup

  1. temperaturecooling
  2. stirringthe resulting mixture was stirred at room temperature for 45 minutes
  3. stirringAfter stirring
  4. extractionextracted with dichloromethane
  5. dry with materialThe extract was dried over anhydrous magnesium sulfate
  6. customThe solvent was removed in vacuo
  7. customthe residue was purified by chromatography on a silica gel column

Sources & evidence

ORD record
ord-698c3f924c17434b8b7d535ad0ada377
Source dataset
uspto-grants-2010_11
Patent number
US07829580B2

Reaction notes

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